Hydrochloric Acid → 3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enenitrile

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Reaction Steps

In a 100 mL-volume glass flask equipped with a stirrer, a thermometer and a dropping funnel were placed under argon atmosphere 1.94 g (6.66 mmol) of 2-cyclo-propyl-4-(4-fluorophenyl)quinoline-3-carbaldehyde, 10 mL of acetonitrile and 0.422 g (10.6 mmol). of sodium hydride (purity: 60%). The content was stirred at room temperature for 2 hours. The resulting mixture was chilled to −10° C. To the chilled mixture was added 20 mL (248 mmol) of ethyl formate, and the mixture was stirred for 4 hours at the same temperature. Subsequently, to the mixture was slowly added 11 mL of hydrochloric acid (1 mol/L) which was previously chilled in an ice bath. In the mixture, an organic portion separated from an aqueous portion. The organic portion was taken out, washed with two 10 mL portions of saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The organic portion was filtered and analyzed by high performance liquid chromatography (absolute quantitative analysis). It was confirmed that 1.71 g (yield: 85%) of 3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enenitrile was produced. The organic portion was concentrated under reduced pressure to leave a yellow solid residue. The solid residue was recrystallized from toluene/hexane (1/8, vol. ratio) to obtain 1.79 g of 3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enenitrile as a yellow crystalline product (purity: 97%). The obtained 3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enenitrile had the following characteristics:

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